Production of monochloro-substituted saturated compounds

Abstract

Monochloro-substituted saturated compounds are prepared by condensing an aliphatic saturated hydrocarbon containing a secondary of tertiary carbon atom with a monochloromonoolefin possessing up to 14 carbon atoms and having the chlorine atom attached to one of the doubly-bonded carbon atoms in the presence of a free radical-generating catalyst.

We claim as our invention: 
     
       1. In a process for producing a monochloro-substituted saturated compound by condensing an acyclic aliphatic saturated hydrocarbon containing a secondary or tertiary carbon atom with a monochloromonoolefin possessing up to 14 carbon atoms and having the chlorine atom attached to one of the doubly-bonded carbon atoms in the presence of a free radical-generating peroxide catalyst at a temperature at least as high as the decomposition temperature of the free radical catalyst and a pressure of from about 1 atmosphere to about 100 atmospheres, and recovering the resultant monochloro-substituted saturated compound, the improvement which comprises effecting said condensation in the presence of a promoter comprising hydrogen chloride. 
     
     
       2. The process of claim 1 further characterized in that the peroxy catalyst is di-t-butyl peroxide. 
     
     
       3. The process of claim 1 further characterized in that hydrogen chloride is anhydrous. 
     
     
       4. The process of claim 1 further characterized in that the hydrogen chloride is aqueous. 
     
     
       5. The process of claim 1 further characterized in that the aliphatic saturated hydrocarbon is isopentane, the monochloromonoolefin is vinyl chloride and the monochloro substituted saturated compound is 1-chloro-3,3-dimethylpentane. 
     
     
       6. The process of claim 1 further characterized in that the aliphatic saturated hydrocarbon is propane, the monochloromonoolefin is 1-chlorocyclopentene-1 and the monochloro-substituted saturated compound is 2-(2-chlorocyclopentyl)propane. 
     
     
       7. The process of claim 1 further characterized in that the aliphatic saturated hydrocarbon is heptane, the monochloromonoolefin is vinyl chloride and the monochloro substituted saturated compound is 2-(2-chloroethyl)heptane. 
     
     
       8. The process of claim 1 further characterized in that the aliphatic saturated hydrocarbon is isopentane, the monochloromonoolefin is 1-chlorotetradecene-1 and the monochloro-substituted saturated compound is 4-chloromethyl-3,3-dimethylhexadecane. 
     
     
       9. The process of claim 1 further characterized in that the aliphatic saturated hydrocarbon is 3-methylpentane, the monochloromonoolefin is vinyl chloride and the monochloro substituted saturated compound is 1-chloro-3-methyl-3-ethyl-pentane.